Security is not a hard-&-fast state. It is a finding a level of acceptable risk. Without knowing anything about what your security goals are, it is very difficult to comment on whether your proposed topology meets those needs.

Quote:

Tor

Personally, relying on a third-party infrastructure (historically with imperfections...) is putting great faith in something in which you have no control.

tor doesn't encrypt , it anonymises traffic ..
my curiosity to learn about @Ocicat's, @Jgimmi's, and @carpetsmoker;s respective predilections for anonymy & encryption .. is limitless .. what tool ? what strategy ? I know from earlier posts that all three hackers don't favour security through obscurity nor do they trust tor network .. working with pf is the choice I guess ..

"Tor aims to conceal its users' identities and their network activity from surveillance and traffic analysis by separating identification and routing. It is an implementation of onion routing, which encrypts and then randomly bounces communications through a network of relays run by volunteers throughout the globe. These onion routers employ encryption in a multi-layered manner (hence the onion metaphor) to ensure perfect forward secrecy between relays, thereby providing users with anonymity in network location."

It is an implementation of onion routing, which encrypts and then randomly bounces communications...

Tor attempts to encrypt packets, but this has no relation to encrypting the fundamental disk. If you believe that Tor will provide you security, let me have physical access to your system, & I will prove the thought otherwise.

OpenBSD does allows portions of secondary store to be encrypted through bioctl(8), but this was not the original question.

As I have referenced elsewhere, Tor's attempt to equate anonymity with privacy is not flawless nor necessarily trustworthy:

Likewise, searching through the archives of the OpenBSD project's mailing lists does not show that the project developers there are strong advocates of Tor either. A question you need to answer to yourself is why is this the case?

@Ocicat , thanks for providing the link again ..
<< .... The Tor website even says:
Yes, the guy running the exit node can read the bytes that come in and out there. Tor anonymizes the origin of your traffic, and it makes sure to encrypt everything inside the Tor network, but it does not magically encrypt all traffic throughout the internet.

Tor anonymizes, nothing more. >>

just an off-topic question : is Schneier involved with any of the BSDs projects ?

Hi @feredim-924 !
the first isn't mine but torproject's ..
am I wrong to say that part of what privacy comes to mean is being able to keep one's identity as well as data private over networks .. while you are centered on your pc security , someome else is centered on the privacy of transmitted data over the network .. does it make a sense ?
the last 2 lines of the page :
<< As long as Tor is a magnet for "interesting" traffic, Tor will also be a magnet for those who want to eavesdrop on that traffic -- especially because more than 90 percent of Tor users don't encrypt. >>